1. Asymmetric Total Synthesis of (-)-(3R)-Inthomycin C.
- Author
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Balcells, Sandra, Haughey, Maxwell B., Walker, Johannes C. L., Josa-Culleré, Laia, Towers, Christopher, and Donohoe, Timothy J.
- Subjects
- *
OLEFINATION reactions , *CHEMICAL reactions , *STOICHIOMETRIC combustion , *CANCER cell analysis , *BOND formation mechanism - Abstract
A short (10 step) and efficient (15% overall yield) synthesis of the natural product (-)-(3R)-inthomycin C is reported. The key steps comprise three C-C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama-Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin-promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (-)-(3R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time. [ABSTRACT FROM AUTHOR]
- Published
- 2018
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